US4731319A - Positive-working naphthoquinone diazide photoresist composition with two cresol novolac resins - Google Patents

Positive-working naphthoquinone diazide photoresist composition with two cresol novolac resins Download PDF

Info

Publication number
US4731319A
US4731319A US06/886,839 US88683986A US4731319A US 4731319 A US4731319 A US 4731319A US 88683986 A US88683986 A US 88683986A US 4731319 A US4731319 A US 4731319A
Authority
US
United States
Prior art keywords
cresol
cresol novolac
weight
photoresist composition
novolac resin
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US06/886,839
Other languages
English (en)
Inventor
Hidekatsu Kohara
Hatsuyuki Tanaka
Masanori Miyabe
Yoshiaki Arai
Shingo Asaumi
Toshimasa Nakayama
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Tokyo Ohka Kogyo Co Ltd
Original Assignee
Tokyo Ohka Kogyo Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Tokyo Ohka Kogyo Co Ltd filed Critical Tokyo Ohka Kogyo Co Ltd
Assigned to TOKYO OHKA KOGYO CO., LTD. reassignment TOKYO OHKA KOGYO CO., LTD. ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: ARAI, YOSHIAKI, ASAUMI, SHINGO, KOHARA, HIDEKATSU, MIYABE, MASANORI, NAKAYAMA, TOSHIMASA, TANAKA, HATSUYUKI
Application granted granted Critical
Publication of US4731319A publication Critical patent/US4731319A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Images

Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/022—Quinonediazides
    • G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
    • G03F7/0233—Macromolecular quinonediazides; Macromolecular additives, e.g. binders characterised by the polymeric binders or the macromolecular additives other than the macromolecular quinonediazides
    • G03F7/0236—Condensation products of carbonyl compounds and phenolic compounds, e.g. novolak resins

Definitions

  • the present invention relates to a positive-working photoresist composition or, more particularly, to a positive-working photoresist composition suitable for use in fine patterning of a photoresist layer in the manufacturing process of semiconductor-based devices such as integrated circuits.
  • the minimum line width to be reproduced with high fidelity in the photoresist layer is about 2 ⁇ m in 256 kilobits DRAMs, about 1.0 to 1.3 ⁇ m in 1 megabit DRAMs and about 0.7 to 0.8 ⁇ m in 4 megabits DRAMs.
  • the patterning works on the semiconductor wafers for the manufacture of integrated circuits are performed by the technology of photolithography using a photoresist composition.
  • a photoresist composition including positive-working and negative-working ones, the positive-working photoresist compositions are preferred widely in the works of fine patterning in which high-fidelity reproduction of a line pattern having a width of 1 to 2 ⁇ m is essential.
  • the principal ingredients in most of the conventional positive-working photoresist compositions are an alkali-soluble novolac resin as the film-forming constituent and a quinone diazide compound as the photodecomposable or photosensitive constituent in the form of a mixture or a condensation product of both. Since the sensitivity, resolving power, etc. in the patterning work heavily depend on the kinds and proportion of these two constituents and the manner of combining them in the photoresist composition as well as on the procedure of development after exposure to light, various attempts and proposals have been made hitherto in respect of manufacturing of the photoresist compositions and the way of using the photoresist composition in the photolithography. For example, Japanese Patent Kokai No.
  • 58-17112 teaches that the sensitivity of a positive-working photoresist composition comprising a cresol novolac resin as the film-forming constituent can be improved by suitably selecting the proportion of the cresol isomers in the cresol used in the preparation of the cresol novolac resin.
  • the exposure is carried out either by the exposure by direct contacting or by the exposure by minifying projection.
  • the photoresist layer formed on the surface of a semiconductor wafer is exposed to light through a patterned photomask in direct contact with the photoresist layer.
  • This method is advantageous in respect of the contrast of the patterned image so that a patterned photoresist layer of a considerably high contrast can be obtained by this method even when the photoresist composition used there is inherently inferior in respect of the contrast and fidelity of the pattern reproduction.
  • this method has some disadvantages and problems.
  • the photomask is sometimes damaged mechanically as a natural consequence of direct contact with the photoresist layer in each time of exposure so that extreme care is required in handling the photomask and good quality of the photomasks can be maintained only with expenses more than negligible.
  • the pattern on the photomask must be of the full-size relative to the pattern to be reproduced so that a patterned photomask having such a high precision is unavoidably very expensive, especially, when the line width of the pattern is in the submicron range.
  • the dimension of the pattern on a patterned photomask can be as large as 5 to 10 times of that in the photoresist pattern to be reproduced so that even a photomask of high precision for patterning in the submicron range can be obtained with a relatively low cost.
  • this method is disadvantageous in respect of the contrast of light between the areas to be exposed and not to be exposed in comparison with the exposure by direct contacting of the photomasks. Therefore, this method of exposure by minifying projection is applicable to the reproduction of a pattern of high precision only when the photoresist composition is inherently suitable for exposure with high contrast or high fidelity.
  • the pattern to be formed in the photoresist layer is not composed of lines having one and the same line width but includes lines having varied line widths combined in a complicated manner. This fact causes a difficult problem affecting the quality of pattern reproduction since the optimum exposure dose to a photoresist layer considerably depends on the line width. Taking the optimum exposure dose to a pattern of 2.0 ⁇ m line width as unity, for example, the optimum exposure doses to patterns of 1.5 ⁇ m and 1.0 ⁇ m line widths are 1.2 to 1.3 and 1.5 to 1.7, respectively.
  • an exposure dose which may be optimum for a line of 1.0 ⁇ m line width is excessively large for lines having line widths of 1.5 and 2.0 ⁇ m in the same pattern so that the fidelity of pattern reproduction cannot be highest over whole area of the pattern.
  • the surface of a semiconductor device under way of processing is not completely flat but usually has a stepwise height difference of 0.5 to 1.0 ⁇ m from portion to portion so that the thickness of a photoresist layer formed on such a stepwise surface cannot be uniform to be smaller in the upside area of the step and larger in the downside area of the step.
  • the line width of the pattern reproduced in the photoresist layer is smaller in the area where the photoresist layer has a smaller thickness than in the area where the thickness is larger affecting the fidelity of pattern reproduction.
  • the above described problems each concern the poor reproducibility or fidelity between the original of the pattern on the photomask and the patterned image reproduced in the photoresist layer.
  • the reasons therefor include, as is mentioned above, the decrease in the contrast in the exposure by minifying projection between the exposed and unexposed areas, difference in the optimum exposure doses between line patterns having different line widths, difference in the film thickness of the photoresist layer between the areas on both sides of a step on the wafer surface having stepwise height differences, and so on.
  • the reproduced line pattern should have a line width which is an accurate reproduction of the line on the original pattern of the photomask without expansion or diminishment irrespective of the exposure dose or the extent of development.
  • the patterned line of the photoresist layer should have a rectangular cross section standing on the substrate surface with definitely angled shoulders while undesirable cross sectional configurations include those having rounded shoulders or having trailing skirts on the substrate surface even with definitely angled shoulders.
  • An object of the present invention is therefore to provide a positive-working photoresist composition free from the above described problems capable of giving a patterned photoresist layer which is an accurate reproduction of the original pattern with high fidelity and unaffected by the influence of the exposure dose on the width of the patterned lines.
  • the positive-working photoresist composition provided by the invention comprises:
  • A-1) a first cresol novolac resin having a weight-average molecular weight of at least 5000 and produced from an isomeric mixture composed of 60 to 80% of m-cresol and 40 to 20% of p-cresol;
  • (A-2) a second cresol novolac resin having a weight-average molecular weight not exceeding 5000 and produced from an isomeric mixture composed of 10 to 40% of m-cresol and 90 to 60% of p-cresol,
  • the overall cresol moiety in the component (A) is composed of from 30 to 46.5% of the m-cresol moiety and from 70 to 53.5% of the p-cresol moiety.
  • FIGS. 1, 2 and 3 each schematically illustrate a cross section of a patterned line of the photoresist layer produced in Examples.
  • the most characteristic feature of the inventive photoresist composition consists in the specific cresol novolac resin as the film-forming constituent which is a combination in a specified proportion of two different cresol novolac resins differentiated in respects of the weight-average molecular weight and the mixing ratio of the m- and p-isomers of cresol used as the starting material for the preparation of the respective cresol novolac resins.
  • fraction of the cresol novolac resin rich in the p-cresol moiety may act as a dissolution retarder in a photoresist layer formulated with the cresol novolac resin and that, therefore, substantial improvements of a photoresist composition can be achieved when the film-forming constituent therein is a combination in a specific proportion of a first cresol novolac resin of a relatively high molecular weight and rich in the m-cresol moiety and a second cresol novolac resin of a relatively low molecular weight and rich in the p-cresol moiety.
  • the naphtoquinone diazide sulfonic acid ester, i.e. component (B), as the photosensitive ingredient in the inventive photoresist composition is a reaction product obtained by the esterification reaction of a naphthoquinone diazide sulfonic acid and a phenolic compound such as polyhydroxy benzophenones, alkyl gallates and the like and the reaction of esterification can be performed readily according to a conventional procedure.
  • the cresol novolac resin, i.e. component (A), as the film-forming constituent in the inventive photoresist composition is, as is mentioned above, a binary combination in a specified proportion of two different cresol novolac resins defined as (A-1) and (A-2) in terms of the weight-average molecular weight and the isomeric mixing ratio of cresol isomers in the starting cresol used in the preparation of the respective cresol novolac resins.
  • the inventive photoresist composition should comprise from 25 to 60 parts by weight of the naphthoquinone diazide sulfonic acid ester as the photosensitive constituent per 100 parts by weight of the cresol novolac resin as the film-forming constituent.
  • the photoresist composition would have a remarkably decreased sensitivity while, when the amount thereof is too small, an adverse effect is caused on the cross sectional configuration of the line in the patterned photoresist layer.
  • the inventive positive-working photoresist composition is used usually in the form of a solution prepared by dissolving the above described cresol novolac resin and the naphthoquinone diazide sulfonic acid ester in a suitable organic solvent.
  • a suitable organic solvent e.g. acetone, methyl ethyl ketone, cyclohexanone and isoamyl ketone, polyhydric alcohols and derivatives thereof, e.g.
  • organic solvents can be used either singly or as a mixture of two kinds or more according to need.
  • inventive positive-working photoresist composition may be admixed optionally with various kinds of known additives having compatibility with the essential ingredients and conventionally used in photoresist compositions such as auxiliary resins, plasticizers, stabilizers, coloring agents to serve for further increasing the visibility of the patterned image after development and so on.
  • additives having compatibility with the essential ingredients and conventionally used in photoresist compositions such as auxiliary resins, plasticizers, stabilizers, coloring agents to serve for further increasing the visibility of the patterned image after development and so on.
  • the procedure for forming a patterned photoresist layer using the inventive photoresist composition may be conventional.
  • the surface of a substrate body such as a semiconductor silicon wafer is coated with the inventive photoresist composition in the form of an organic solution by use of a suitable coating machine such as spinners followed by drying to form a uniform photoresist layer thereon, which is then exposed to light on a minifying projector or a suitable apparatus for exposure through a photomask bearing a desired pattern followed by development using a developing solution such as an aqueous solution of an organic base, e.g.
  • the inventive positive-working photoresist composition can be used advantageously in the manufacture of high-precision semiconductor devices such as VLSIs.
  • a positive-working photoresist composition in the form of a solution was prepared by dissolving 30 parts by weight of the resin I, 70 parts by weight of the resin II and 30 parts by weight of a reaction product of 2,3,4-trihydroxy benzophenone and naphthoquinone-1,2-diazide-5-sulfonic chloride in a molar ratio of 1:1.6 in 390 parts by weight of ethylene glycol monoethyl ether acetate followed by filtration through a membrane filter having pores of 0.2 ⁇ m diameter.
  • a silicon wafer of 3 inch diameter was uniformly coated with the photoresist solution in a coating thickness of 1.3 ⁇ m as dried using a resist coater (Model TR-4000, manufactured by Tazmo Co.) followed by drying and pre-baking for 90 seconds on a hot plate kept at 110° C. to give a photoresist layer on the wafer.
  • the silicon wafer provided with the photoresist coating layer was then exposed to ultraviolet light on a minifying projector (Wafer Stepper Model DSW-4800, manufactured by GCA Co.) through a test chart photomask manufactured by Dai-Nippon Printing Co. and developed for 30 seconds at 23° C. using a 2.38% by weight aqueous solution of tetramethyl ammonium hydroxide as the developing solution.
  • the patterned lines of the photoresist layer thus developed had an ideally rectangular cross section as is schematically illustrated in FIG. 1 of the accompanying drawing.
  • the experimental procedure was substantially the same as in Example 1 except that the m-cresol-rich cresol novolac resin, referred to as the resin I hereinbelow, and the p-cresol-rich cresol novolac resin, referred to as the resin II hereinbelow, used in each of the experiments were each prepared from an isomeric mixture of m-and p-cresols in a proportion shown in Table 1 below as the m:p ratio and had a weight-average molecular weight also shown in the table as M w , that the resins I and II were taken each in an amount shown in the table by parts by weight to give a weight ratio of the m-cresol moiety to the p-cresol moiety in the combined cresol novolac resins shown in the table as the overall m:p ratio and that different photosensitive compounds were used in varied amounts as indicated in the table.
  • the photosensitizer components are indicated by the symbols respectively indicating the following compounds.
  • the ratio of OH:AZ given in the table is defined by the molar ratio of the phenolic compound and the naphthoquinone diazide compound taken as the starting materials in the esterification reaction for the preparation of the respective photosensitive compounds.
  • the experimental procedure was substantially the same as in Comparative Example 1 except that the test chart photomask was replaced with the same test chart reticle as used in Example 9 and the length of the exposure time was 450 milliseconds.
  • the results were that the line-and-space pattern of 1.25 ⁇ m width could be reproduced on the silicon wafer while the line-and-space pattern of 2.0 ⁇ m width was reproduced incompletely as composed of a line pattern of 1.6 ⁇ m width and a space pattern of 2.4 ⁇ m width.

Landscapes

  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Materials For Photolithography (AREA)
  • Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
US06/886,839 1985-08-09 1986-07-18 Positive-working naphthoquinone diazide photoresist composition with two cresol novolac resins Expired - Lifetime US4731319A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP60-174314 1985-08-09
JP60174314A JPH0654384B2 (ja) 1985-08-09 1985-08-09 ポジ型ホトレジスト組成物

Publications (1)

Publication Number Publication Date
US4731319A true US4731319A (en) 1988-03-15

Family

ID=15976485

Family Applications (1)

Application Number Title Priority Date Filing Date
US06/886,839 Expired - Lifetime US4731319A (en) 1985-08-09 1986-07-18 Positive-working naphthoquinone diazide photoresist composition with two cresol novolac resins

Country Status (4)

Country Link
US (1) US4731319A (de)
JP (1) JPH0654384B2 (de)
DE (1) DE3626578A1 (de)
GB (1) GB2181441B (de)

Cited By (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4882260A (en) * 1986-06-16 1989-11-21 Tokyo Ohka Kogyo Co., Ltd. Positive-working photosensitive quinone diazide composition with alkali insoluble dye and alkali soluble dye
US4985333A (en) * 1988-04-22 1991-01-15 Tokyo Ohka Kogyo Co., Ltd. Positive-working photosensitive composition with three difference 1,2-naphthoquinone diazide sulfonic acid esters to include the ester of curcumin
US4988601A (en) * 1987-11-26 1991-01-29 Kabushiki Kaisha Toshiba Photosensitive resin composition with o-quinone diazide and novolac resins prepared from mixed phenolic reactants to include 3,5-xylenol and 2,5-xylenol
US4996122A (en) * 1988-03-31 1991-02-26 Morton International, Inc. Method of forming resist pattern and thermally stable and highly resolved resist pattern
WO1991003448A1 (en) * 1989-09-07 1991-03-21 Ocg Microelectronic Materials, Inc. Selected block phenolic oligomers and their use in phenolic resin compositions and in radiation-sensitive resist compositions
WO1991004512A1 (en) * 1989-09-07 1991-04-04 Ocg Microelectronic Materials, Inc. Selected block copolymer novolak binder resins and their use in radiation-sensitive compositions
US5023311A (en) * 1985-12-06 1991-06-11 Toray Industries, Inc. High-molecular-weight soluble novolak resin and process for preparation thereof
US5080997A (en) * 1988-12-06 1992-01-14 Sumitomo Chemical Company, Limited Process for preparing a positive resist composition by mixing the condensation product of a quinone diazide sulfonyl halogenide and a phenol with a resin solution without isolating the condensation product from the crude mixture
US5188921A (en) * 1989-09-07 1993-02-23 Ocg Microelectronic Materials, Inc. Selected block copolymer novolak binder resins in radiation-sensitive resist compositions
US5196289A (en) * 1989-09-07 1993-03-23 Ocg Microelectronic Materials, Inc. Selected block phenolic oligomers and their use in radiation-sensitive resist compositions
US5232819A (en) * 1989-09-07 1993-08-03 Ocg Microelectronic Materials, Inc. Selected block phenolic oligomers and their use in phenolic resin compositions and in radiation-sensitive resist compositions
US5234795A (en) * 1989-09-07 1993-08-10 Ocg Microelectronic Materials, Inc. Process of developing an image-wise exposed resist-coated substrate
US5266440A (en) * 1986-12-23 1993-11-30 Shipley Company Inc. Photoresist composition with aromatic novolak binder having a weight-average molecular weight in excess of 1500 Daltons
US5281508A (en) * 1985-08-09 1994-01-25 Tokyo Ohka Kogyo Co., Ltd. Positive-working photoresist containing o-naphthoquinone diazide sulfonic acid ester and novolak resin consisting of 35 to 43% m-cresol and 65 to 57% p-cresol with substantial absence of o-cresol
US5290658A (en) * 1991-04-26 1994-03-01 Fuji Photo Film Co., Ltd. Positive type photoresist composition comprising polyaromatic hydroxy quinone diazide esters as the photosensitive ingredient
US5302490A (en) * 1991-10-21 1994-04-12 Shipley Company Inc. Radiation sensitive compositions comprising blends of an aliphatic novolak resin and an aromatic novolak resin
US5306596A (en) * 1989-11-17 1994-04-26 Nippon Zeon Co., Ltd. Positive resist composition comprising a polyphenolic o-quinone diazide sulfonate
US5326665A (en) * 1992-03-05 1994-07-05 Sumitomo Chemical Company, Limited Positive type resist composition
US5342727A (en) * 1988-10-21 1994-08-30 Hoechst Celanese Corp. Copolymers of 4-hydroxystyrene and alkyl substituted-4-hydroxystyrene in admixture with a photosensitizer to form a photosensitive composition
US5374693A (en) * 1992-12-29 1994-12-20 Hoechst Celanese Corporation Novolak resin blends for photoresist applications
US5403696A (en) * 1990-02-23 1995-04-04 Sumitomo Chemical Company, Limited Radiation-sensitive positive resist composition comprising an alkali-soluble resin made from tert-butyl-methyl phenol
US5407780A (en) * 1989-12-27 1995-04-18 Sumitomo Chemical Company, Limited Radiation-sensitive positive resist composition comprising an alkali-soluble resin made from m-cresol, 2-tert-butl-5-methyl phenol and formaldehyde
US5413895A (en) * 1991-08-21 1995-05-09 Sumitomo Chemical Company, Limited Positive resist composition comprising a quinone diazide sulfonic acid ester, a novolak resin and a polyphenol compound.
US5413894A (en) * 1993-05-07 1995-05-09 Ocg Microelectronic Materials, Inc. High ortho-ortho bonded novolak binder resins and their use in radiation-sensitive compositions
US5429904A (en) * 1992-05-27 1995-07-04 Sumitomo Chemical Company, Ltd. Positive resist composition
US5451484A (en) * 1992-05-27 1995-09-19 Sumitomo Chemical Company, Ltd. Positive resist composition
US5478691A (en) * 1988-10-18 1995-12-26 Japan Synthetic Rubber Co., Ltd. Radiation-sensitive resin composition
US5736292A (en) * 1989-08-24 1998-04-07 Sumitomo Chemical Company, Limited Radiation-sensitive positive resist composition comprising an alkali soluble resin made from m-cresol, 2,3,5-trimethyl phenol and optionally p-cresol and a polyphenol compound having alkyl or alkoxy side groups
US20020146645A1 (en) * 1999-08-25 2002-10-10 Toshikazu Tachikawa Multilayered body for photolithographic patterning
US6506441B2 (en) 1998-12-20 2003-01-14 Honeywell International Inc. Novolac polymer planarization films with high temperature stability
WO2003085045A1 (en) * 2002-04-11 2003-10-16 Clariant International Ltd Novolak resin mixtures and photosensitive compositions comprising the same
CN1313882C (zh) * 2003-04-04 2007-05-02 东京应化工业株式会社 排出喷嘴式涂布法用正型光致抗蚀剂组合物以及抗蚀图的形成方法
CN100351701C (zh) * 2003-09-30 2007-11-28 东京应化工业株式会社 排出喷嘴式涂布法用正型光致抗蚀剂组合物以及抗蚀图案的形成方法
US20090227058A1 (en) * 2008-03-04 2009-09-10 Samsung Electronics Co., Ltd. Photoresist composition and method of manufacturing array substrate using the same
US20140363915A1 (en) * 2013-06-11 2014-12-11 Chi Mei Corporation Negative photosensitive resin composition and application thereof
US20200089114A1 (en) * 2018-09-13 2020-03-19 Echem Solutions Corp. Positive photoresist composition and method of forming patterned polyimide layer
US11531268B2 (en) 2017-07-31 2022-12-20 Lg Chem, Ltd. Positive-working photoresist composition, pattern produced therefrom, and method for producing pattern

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0654391B2 (ja) * 1987-03-06 1994-07-20 住友化学工業株式会社 電子線又はｘ線用ポジ型レジスト組成物
EP0293704A3 (de) * 1987-06-01 1989-02-15 Hoechst Celanese Corporation Aufzeichnungsmaterial mit einer wasserlöslichen Kontrastverstärkungsschicht
JP2623778B2 (ja) * 1988-10-18 1997-06-25 日本合成ゴム株式会社 感放射線性樹脂組成物
JP2554760B2 (ja) * 1990-01-11 1996-11-13 東京応化工業株式会社 ポジ型ホトレジスト組成物
US5371169A (en) * 1992-09-28 1994-12-06 Hoechst Celanese Corporation Novolak resin mixtures
JP3562673B2 (ja) 1996-01-22 2004-09-08 富士写真フイルム株式会社 ポジ型フォトレジスト組成物

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4377631A (en) * 1981-06-22 1983-03-22 Philip A. Hunt Chemical Corporation Positive novolak photoresist compositions
US4404357A (en) * 1982-05-03 1983-09-13 Shipley Company Inc. High temperature naphthol novolak resin
EP0118291A2 (de) * 1983-03-04 1984-09-12 Sumitomo Chemical Company, Limited Photoschutzschicht-Zusammensetzungen mit "Novolak"-Kunststoff
JPS6042753A (ja) * 1983-08-17 1985-03-07 Mitsubishi Chem Ind Ltd ポジ型クレゾ−ルノボラツクフオトレジスト組成物
US4551409A (en) * 1983-11-07 1985-11-05 Shipley Company Inc. Photoresist composition of cocondensed naphthol and phenol with formaldehyde in admixture with positive o-quinone diazide or negative azide
JPS616647A (ja) * 1984-06-20 1986-01-13 Konishiroku Photo Ind Co Ltd ポジ型感光性平版印刷版用感光性組成物
US4587196A (en) * 1981-06-22 1986-05-06 Philip A. Hunt Chemical Corporation Positive photoresist with cresol-formaldehyde novolak resin and photosensitive naphthoquinone diazide

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2616992C3 (de) * 1976-04-17 1987-10-22 Agfa-Gevaert Ag, 5090 Leverkusen Lichtempfindliches Kopiermaterial zur Herstellung von Reliefs
JPS561045A (en) * 1979-06-16 1981-01-08 Konishiroku Photo Ind Co Ltd Photosensitive composition
JPS5817112A (ja) * 1981-06-22 1983-02-01 フイリツプ・エイ・ハント・ケミカル・コ−ポレイシヨン ポジ型ノボラツクホトレジスト組成物及びその調製物
JPS61144644A (ja) * 1984-12-19 1986-07-02 Japan Synthetic Rubber Co Ltd ポジ型感放射線樹脂組成物

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4377631A (en) * 1981-06-22 1983-03-22 Philip A. Hunt Chemical Corporation Positive novolak photoresist compositions
US4587196A (en) * 1981-06-22 1986-05-06 Philip A. Hunt Chemical Corporation Positive photoresist with cresol-formaldehyde novolak resin and photosensitive naphthoquinone diazide
US4404357A (en) * 1982-05-03 1983-09-13 Shipley Company Inc. High temperature naphthol novolak resin
EP0118291A2 (de) * 1983-03-04 1984-09-12 Sumitomo Chemical Company, Limited Photoschutzschicht-Zusammensetzungen mit "Novolak"-Kunststoff
JPS6042753A (ja) * 1983-08-17 1985-03-07 Mitsubishi Chem Ind Ltd ポジ型クレゾ−ルノボラツクフオトレジスト組成物
US4551409A (en) * 1983-11-07 1985-11-05 Shipley Company Inc. Photoresist composition of cocondensed naphthol and phenol with formaldehyde in admixture with positive o-quinone diazide or negative azide
JPS616647A (ja) * 1984-06-20 1986-01-13 Konishiroku Photo Ind Co Ltd ポジ型感光性平版印刷版用感光性組成物

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Pampalone, T. R., Solid State Technology, 6/1984, pp. 115 120. *
Pampalone, T. R., Solid State Technology, 6/1984, pp. 115-120.

Cited By (48)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5792585A (en) * 1898-10-05 1998-08-11 Sumitomo Chemical Company, Limited Radiation-sensitive positive resist composition
US5281508A (en) * 1985-08-09 1994-01-25 Tokyo Ohka Kogyo Co., Ltd. Positive-working photoresist containing o-naphthoquinone diazide sulfonic acid ester and novolak resin consisting of 35 to 43% m-cresol and 65 to 57% p-cresol with substantial absence of o-cresol
US5023311A (en) * 1985-12-06 1991-06-11 Toray Industries, Inc. High-molecular-weight soluble novolak resin and process for preparation thereof
US4882260A (en) * 1986-06-16 1989-11-21 Tokyo Ohka Kogyo Co., Ltd. Positive-working photosensitive quinone diazide composition with alkali insoluble dye and alkali soluble dye
US5266440A (en) * 1986-12-23 1993-11-30 Shipley Company Inc. Photoresist composition with aromatic novolak binder having a weight-average molecular weight in excess of 1500 Daltons
US4988601A (en) * 1987-11-26 1991-01-29 Kabushiki Kaisha Toshiba Photosensitive resin composition with o-quinone diazide and novolac resins prepared from mixed phenolic reactants to include 3,5-xylenol and 2,5-xylenol
US4996122A (en) * 1988-03-31 1991-02-26 Morton International, Inc. Method of forming resist pattern and thermally stable and highly resolved resist pattern
US4985333A (en) * 1988-04-22 1991-01-15 Tokyo Ohka Kogyo Co., Ltd. Positive-working photosensitive composition with three difference 1,2-naphthoquinone diazide sulfonic acid esters to include the ester of curcumin
US5478691A (en) * 1988-10-18 1995-12-26 Japan Synthetic Rubber Co., Ltd. Radiation-sensitive resin composition
US5342727A (en) * 1988-10-21 1994-08-30 Hoechst Celanese Corp. Copolymers of 4-hydroxystyrene and alkyl substituted-4-hydroxystyrene in admixture with a photosensitizer to form a photosensitive composition
US5080997A (en) * 1988-12-06 1992-01-14 Sumitomo Chemical Company, Limited Process for preparing a positive resist composition by mixing the condensation product of a quinone diazide sulfonyl halogenide and a phenol with a resin solution without isolating the condensation product from the crude mixture
US5783355A (en) * 1989-08-24 1998-07-21 Sumitomo Chemical Company, Limited Radiation-sensitive positive resist composition
US5736292A (en) * 1989-08-24 1998-04-07 Sumitomo Chemical Company, Limited Radiation-sensitive positive resist composition comprising an alkali soluble resin made from m-cresol, 2,3,5-trimethyl phenol and optionally p-cresol and a polyphenol compound having alkyl or alkoxy side groups
US5234795A (en) * 1989-09-07 1993-08-10 Ocg Microelectronic Materials, Inc. Process of developing an image-wise exposed resist-coated substrate
US5188921A (en) * 1989-09-07 1993-02-23 Ocg Microelectronic Materials, Inc. Selected block copolymer novolak binder resins in radiation-sensitive resist compositions
US5232819A (en) * 1989-09-07 1993-08-03 Ocg Microelectronic Materials, Inc. Selected block phenolic oligomers and their use in phenolic resin compositions and in radiation-sensitive resist compositions
US5196289A (en) * 1989-09-07 1993-03-23 Ocg Microelectronic Materials, Inc. Selected block phenolic oligomers and their use in radiation-sensitive resist compositions
WO1991003448A1 (en) * 1989-09-07 1991-03-21 Ocg Microelectronic Materials, Inc. Selected block phenolic oligomers and their use in phenolic resin compositions and in radiation-sensitive resist compositions
WO1991004512A1 (en) * 1989-09-07 1991-04-04 Ocg Microelectronic Materials, Inc. Selected block copolymer novolak binder resins and their use in radiation-sensitive compositions
US5532107A (en) * 1989-11-17 1996-07-02 Nippon Zeon Co., Ltd. Positive resist composition
US5306596A (en) * 1989-11-17 1994-04-26 Nippon Zeon Co., Ltd. Positive resist composition comprising a polyphenolic o-quinone diazide sulfonate
US5407780A (en) * 1989-12-27 1995-04-18 Sumitomo Chemical Company, Limited Radiation-sensitive positive resist composition comprising an alkali-soluble resin made from m-cresol, 2-tert-butl-5-methyl phenol and formaldehyde
US5403696A (en) * 1990-02-23 1995-04-04 Sumitomo Chemical Company, Limited Radiation-sensitive positive resist composition comprising an alkali-soluble resin made from tert-butyl-methyl phenol
US5290658A (en) * 1991-04-26 1994-03-01 Fuji Photo Film Co., Ltd. Positive type photoresist composition comprising polyaromatic hydroxy quinone diazide esters as the photosensitive ingredient
US5413895A (en) * 1991-08-21 1995-05-09 Sumitomo Chemical Company, Limited Positive resist composition comprising a quinone diazide sulfonic acid ester, a novolak resin and a polyphenol compound.
US5302490A (en) * 1991-10-21 1994-04-12 Shipley Company Inc. Radiation sensitive compositions comprising blends of an aliphatic novolak resin and an aromatic novolak resin
US5326665A (en) * 1992-03-05 1994-07-05 Sumitomo Chemical Company, Limited Positive type resist composition
US5429904A (en) * 1992-05-27 1995-07-04 Sumitomo Chemical Company, Ltd. Positive resist composition
US5451484A (en) * 1992-05-27 1995-09-19 Sumitomo Chemical Company, Ltd. Positive resist composition
US5374693A (en) * 1992-12-29 1994-12-20 Hoechst Celanese Corporation Novolak resin blends for photoresist applications
US5473045A (en) * 1993-05-07 1995-12-05 Ocg Microelectronic Materials, Inc. High ortho-ortho bonded novolak binder resins and their use in radiation-sensitive compositions
US5413894A (en) * 1993-05-07 1995-05-09 Ocg Microelectronic Materials, Inc. High ortho-ortho bonded novolak binder resins and their use in radiation-sensitive compositions
US5494785A (en) * 1993-05-07 1996-02-27 Ocg Microelectronic Materials, Inc. High ortho-ortho bonded novolak binder resins and their use in a process for forming positive resist patterns
US6506441B2 (en) 1998-12-20 2003-01-14 Honeywell International Inc. Novolac polymer planarization films with high temperature stability
US6506831B2 (en) 1998-12-20 2003-01-14 Honeywell International Inc. Novolac polymer planarization films with high temperature stability
US6517951B2 (en) 1998-12-20 2003-02-11 Honeywell International Inc. Novolac polymer planarization films with high temperature stability
US20050008972A1 (en) * 1999-08-25 2005-01-13 Toshikazu Tachikawa Multilayered body for photolithographic patterning
US20020146645A1 (en) * 1999-08-25 2002-10-10 Toshikazu Tachikawa Multilayered body for photolithographic patterning
US7033731B2 (en) 1999-08-25 2006-04-25 Tokyo Ohka Kogyo Co., Ltd. Multilayered body for photolithographic patterning
US6733949B2 (en) 2002-04-11 2004-05-11 Clariant Finance (Bvi) Limited Novolak resin mixtures and photosensitive compositions comprising the same
WO2003085045A1 (en) * 2002-04-11 2003-10-16 Clariant International Ltd Novolak resin mixtures and photosensitive compositions comprising the same
CN1313882C (zh) * 2003-04-04 2007-05-02 东京应化工业株式会社 排出喷嘴式涂布法用正型光致抗蚀剂组合物以及抗蚀图的形成方法
CN100351701C (zh) * 2003-09-30 2007-11-28 东京应化工业株式会社 排出喷嘴式涂布法用正型光致抗蚀剂组合物以及抗蚀图案的形成方法
US20090227058A1 (en) * 2008-03-04 2009-09-10 Samsung Electronics Co., Ltd. Photoresist composition and method of manufacturing array substrate using the same
US20140363915A1 (en) * 2013-06-11 2014-12-11 Chi Mei Corporation Negative photosensitive resin composition and application thereof
US11531268B2 (en) 2017-07-31 2022-12-20 Lg Chem, Ltd. Positive-working photoresist composition, pattern produced therefrom, and method for producing pattern
US20200089114A1 (en) * 2018-09-13 2020-03-19 Echem Solutions Corp. Positive photoresist composition and method of forming patterned polyimide layer
US11609496B2 (en) 2018-09-13 2023-03-21 Echem Solutions Corp. Method of forming patterned polyimide layer

Also Published As

Publication number Publication date
DE3626578C2 (de) 1989-03-23
GB2181441A (en) 1987-04-23
JPH0654384B2 (ja) 1994-07-20
JPS6235347A (ja) 1987-02-16
GB2181441B (en) 1988-07-13
DE3626578A1 (de) 1987-02-12
GB8619367D0 (en) 1986-09-17

Similar Documents

Publication Publication Date Title
US4731319A (en) Positive-working naphthoquinone diazide photoresist composition with two cresol novolac resins
US4906549A (en) Positive-working photoresist composition with quinone diazide sulfonic acid ester and novolac made from m-cresol, p-cresol and aliphatic phenol with 2-6 carbon atoms
US4988601A (en) Photosensitive resin composition with o-quinone diazide and novolac resins prepared from mixed phenolic reactants to include 3,5-xylenol and 2,5-xylenol
US4873177A (en) Method for forming a resist pattern on a substrate surface and a scum-remover therefor
US4943511A (en) High sensitivity mid and deep UV resist
US4610953A (en) Aqueous developer solution for positive type photoresists with tetramethyl ammonium hydroxide and trimethyl hydroxyethyl ammonium hydroxide
KR900002362B1 (ko) 포지티브형 감광성 조성물
GB2180842A (en) Positive-working photoresist composition
US4804612A (en) Highly heat-resistant positive-working o-quinone diazide containing photoresist composition with novolac resin made from phenol with ethylenic unsaturation
KR910004844B1 (ko) 포지티브-워킹 포토레지스트 조성물
EP0336605B1 (de) Hochempfindlicher Resist für das mittlere und tiefe UV
US5281508A (en) Positive-working photoresist containing o-naphthoquinone diazide sulfonic acid ester and novolak resin consisting of 35 to 43% m-cresol and 65 to 57% p-cresol with substantial absence of o-cresol
US4985333A (en) Positive-working photosensitive composition with three difference 1,2-naphthoquinone diazide sulfonic acid esters to include the ester of curcumin
JPH0656487B2 (ja) ポジ型ホトレジスト用組成物
US5552255A (en) Article utilizing quinone diazide resist layer on tantalum substrate surface
US5322757A (en) Positive photoresists comprising a novolak resin made from 2,3-dimethyl phenol,2,3,5-trimethylphenol and aldehyde with no meta-cresol present
JP2618947B2 (ja) ポジ型ホトレジスト組成物
US4996122A (en) Method of forming resist pattern and thermally stable and highly resolved resist pattern
US5100758A (en) Positive-working photoresist composition containing quinone diazide compound, novolak resin and alkyl pyruvate solvent
JPH0561195A (ja) ポジ型ホトレジスト組成物
JP2618940B2 (ja) ポジ型ホトレジスト組成物
KR0124949B1 (ko) 감방사선성 수지 조성물
JPS62260145A (ja) ポジ型ホトレジスト組成物
JPH0650395B2 (ja) ポジ型ホトレジスト用組成物
JP2619050B2 (ja) ポジ型感光性組成物

Legal Events

Date Code Title Description
AS Assignment

Owner name: TOKYO OHKA KOGYO CO., LTD., 150, NAKAMARUKO, NAKAH

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNORS:KOHARA, HIDEKATSU;TANAKA, HATSUYUKI;MIYABE, MASANORI;AND OTHERS;REEL/FRAME:004580/0418

Effective date: 19860707

STCF Information on status: patent grant

Free format text: PATENTED CASE

FPAY Fee payment

Year of fee payment: 4

FPAY Fee payment

Year of fee payment: 8

FPAY Fee payment

Year of fee payment: 12